Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.

Septimius The Great

After searching for a purpose or next level in life and experiencing a relationship break-up – I decide to re-invent myself as a music artist. This was a huge risk being that I had no knowledge of the music industry except to urge to be creative. So I jumped into learning the business and performing life of music. Read more>>

Kyler Lyons

While I am very outspoken in my personal life. I had kept myself within the boundaries of what I deemed the safe zone in. When God led me to move to Arizona from the Chicagoland suburbs (where I was born and raised) in 2021, I knew I had to go. That was the hardest step of my journey thus far. When it came time to walk in faith and launch my Podcast. I was much less nervous. I knew absolutely nothing about this field. But I had a newfound grit to me. I had been a consumer of content. But never on the producing end. Being able to encourage and uplift others along the way had made all of the risk worth it. Read more>>

Ted Miller And Alice Miller

Taking a risk…we think the best place to dig into this topic would going back to where it all started for us. Making that initial decision to invest in ourselves was a huge risk in and of itself. There was the monetary risk of taking out a loan to record our very first album, but there was also a risk emotionally. It’s a very vulnerable place to be. We not only worried about if we were making the right decision to go in debt so that we could share our music, but we also worried about how our music would be received. As artists, we realized we needed support and acceptance to recoup our costs and hopefully even make enough to be able to do the whole process again. That means our stories needed to resonate with the listeners. Read more>>

Denice Woller

Stepping away from photographing all genres to specialize in Legacy and High School Senior photography was a huge leap of faith. After nearly two decades of steady, word-of-mouth business, narrowing my focus—and stepping into the world of marketing—felt like starting over. It was risky, especially after building a career without ever needing to promote myself. But I knew this was a step God was calling me to take. Embracing this niche has brought clarity, renewed passion, and a stronger sense of purpose. It’s led to deeper connections and more meaningful experiences—for both me and my clients. Read more>>

Hannah Henriques

In August 2024, I took one of the most significant risks of my life—I left behind the security of my desk job to fully embrace a life of creativity, passion, and entrepreneurial independence. This decision wasn’t easy; the stability of a traditional job offered comfort, but it didn’t align with the vision I had for my future or the kind of parent and individual I wanted to be. Read more>>

Jessica Rolla

I took a big risk to move across the country from the big city of Chicago or Midwest Illinois to here to the quieter mountains here in Northwest Las Vegas or area called Centennial Hills by a nice area called Summerlin in November of 2023.

I was raised and educated in Chicago and the suburb of Darien Illinois with a robust career as a Nanny /Tutor under Datenightboutique luxury caregiver agency and busy Brand ambassador covering a lot of store and tradeshow events. Read more>>

Laura Mignott

When I started my first business, DFlash, it was an idea that we came up with in a Starbucks. It was a simple idea, create an event that we wanted to go to. It quickly became a popular monthly series. What had started as a fun side project, had become a business and I now had to decide whether I should quit my full time job and give this idea a real shot at success. Well, I thought it was worth the risk and took the leap, quitting my job and working on the business full time. Of course, we had no money at the time, so I cashed out my 401k and used those funds to get going. As soon as I went full time at the business, we started to grow and get bigger projects and bigger budgets and more importantly my entrepreneurial life started. Read more>>

LaKesa McGraw

One significant risk I took was launching my life coaching and training business, Inside of Y.O.U., LLC. After over a decade in HR, coaching, and leadership, I knew I had a passion for empowering others. However, stepping away from the stability of my traditional career path to build something from the ground up was daunting. Read more>>

Nicki L. Pete, MA, PLT

I took a significant risk by bringing Skyn 32 Aesthetics Studio to life after years in the corporate world. My journey began in San Francisco with a Fortune 500 company. I later seized the opportunity to join a small team and relocated to Texas. Two years later, the pandemic prompted me to rethink my career, and I realized I wasn’t fulfilled in my work, leading me to retire. Read more>>

Greg Jursek

The biggest risk I took wasn’t starting my business, as it started as a side-hustle. The risk was finally leaving the full-time job with benefits at the most valuable company in the world.

Disc golf isn’t exactly a booming industry but I didn’t leave Apple for Disc Golf because of the money in the sport. I left because I didn’t have the passion anymore at Apple, and I was and still am incredibly passionate about disc golf. Read more>>

Anthony Harrell

Starting my own business has been one of the biggest risks I’ve ever taken, but a path I was always destined for. I’ve always been someone who “wanted more” from life. As a child, I wanted so badly to leave my hometown and explore the world. In college, I did that and was met with a new feeling of not wanting do a typical 9-5 internship. Instead, I became a wildland firefighter and fought fires around the western United States for 3 years. Upon finishing my undergraduate degree, I wanted to test my academic potential so I entered a doctoral program and ended up earning a Doctor of Physical Therapy degree from one of the top 20 programs in the nation. Read more>>

Nicole Engelmann

Looking back I feel the big pivoting moments of my life were always huge risks I took. Moving to London at 22 years old with no family here, savings for 3 months and no real plan, beyond wanting to live in this big, beautiful and noisy city. Turning my hobby into a side hustle and then 2 years later leaving the safety of a 9-5 job (I was an export coordinator in the interior design industry) to turn that side hustle into my full-time business. Read more>>

Marsha Kreho

I’ve learned that sometimes the biggest risks are the ones that ask us to trust ourselves—especially when no one else really gets it. True courage, for me, hasn’t been about fearlessness. It’s been about moving forward with shaky hands, a strong heart, and a quiet voice inside that says, “This is the way.”

At 19, I found out I was pregnant. A lot of people looked at me like it was the end of my story. But I wasn’t scared. The situation wasn’t easy—during my pregnancy, the baby’s father developed a meth addiction, and the relationship became physically abusive. The moment that happened, I left. I knew I’d be raising my baby alone, and strangely, that didn’t terrify me either. Read more>>

Viola Dormann-Tessensohn

I was not born fearless. In fact, for much of my early life, I was the opposite, cautious, uncertain, bound by fear. A premature birth with no brain function predicted. Autism shaping the way I saw the world, forcing me to learn the rules of human interaction rather than instinctively knowing them. I was the child who hesitated, who watched from the sidelines, unsure whether I could step into the arena of life. Read more>>

Yolanda Easton

One of the biggest risks I’ve taken came when I stepped into something completely new, unsure of how—or even if—it would work out.

My husband, a retired Air Force veteran with 32 years of service, and I had always been a team when it came to serving our community. So when he retired, I truly thought that chapter of our lives was over. We were ready for this next season—retirement. We had moved into our forever home, became empty nesters, found a church we loved, and even began traveling. Everything seemed perfect on paper. Read more>>

Ali Keller

There’s a lot of answers to this question. The most recent career risk I’ve taken was participating in the Soho Playhouse Lighthouse Series last year. It was both an artistic and a financial risk.

Soho Playhouse does a great festival every spring/summer where writers can showcase sections of their full length shows to audiences who will then vote on their favorites. If a show gets voted through to the next round, the theater will pick one to produce the following season. Read more>>

Aaron Rokstad

“One of the biggest risks I’ve taken in my career was leaving a stable leadership role at Quanta Services to start Rokstad Power from scratch. I had spent years working my way up, becoming president of one of their subsidiaries, but I realized that public company life wasn’t for me. I wanted to build something on my own terms. Read more>>

Terell Selk

Eleven years ago I made the decision to leave my current community of Red Deer, Alberta and move to Vancouver Island, British Columbia. I was 27 and what did I have to lose? The timeline went for eight weeks to two, which threw me into a mad dash to prep my condo for sale and pack up my life into a car to then make the drive through some rather horrid winter conditions. Read more>>

My very first “bookstagram” post was in August of 2018 and I had no idea that bookstagram even existed. I created a book account as a means to escape a very hard infertility struggle that I was deeply into at the time. My husband said that maybe I should focus my mind on one of my hobbies to help destress and I wept “WHAT HOBBY?!? Eating pizza?! Turning into a couch?!?” And he kindly reminded me that all I do is read. So here I am. I created a book account, posted an intro post, shared some reviews…and well the rest is history. I made some beautifully wonderful and ridiculous lifelong friends that are like family. Read more>>

Tyler Cabrinha

Most of the things ive done in my life took risks, and I believe if your not willing to take them you will never reach goals you may have! I had to risk a lot to become a tattoo artist and sacrifice a lot as well, But for all the risks I took and failed on, the ones that succeeded were exponentially greater than those fails! So many good things in life come out of risks and once u learn to overcome the fear associated with taking them your life and goals will take taking shape. Read more>>

April Mata

In 2017, my then-husband and I rented a building with -$400 in our bank account. Yes, negative. We had accidentally paid our car payment twice, and suddenly, we were in the red. The building, an old speakeasy, had a $3000 monthly rent, but I somehow convinced myself we’d make it work. Why did I believe that? I honestly have no idea. I have always been keen to take risks; I believe that bold results require bold action. So, while everyone, including my bank, said no, I said yes. I took our refund check and made the deposit to start our adventure, and oh, was it an adventure. Read more>>

Richard Taylor

A Risk That Redefined My Business and My Future
In 2014, I took a leap into the unknown. At the time, I was working a steady job, but I had a passion for men’s style and an entrepreneurial drive that wouldn’t let me settle. I decided to start selling accessories—lapel pins, to be exact—online. It was a small risk on the surface, but it felt big to me. I didn’t know if there was a real market for it, and I certainly didn’t know if I could turn it into something sustainable. But I believed in the product, so I pressed forward. Read more>>

Eva Rivera

This question stood out to me because I just had a conversation with some of my closest friends about this. I took a risk in applying for a Master’s program here in San Antonio. I lived in the Rio Grande Valley, in a small town named San Juan. I had just graduated with my Bachelor’s in Rehabilitative Services and I secretly applied for a Marriage and Family Therapy program here in San Antonio. When I say secretly, as in I did not tell anyone about this. I wanted to go through the process on my own and just take the risk of moving to another city, 4 hours away, and accomplish this dream of becoming a Mental Health Professional. Read more>>

Patria Webster

The biggest risk I’ve ever taken was to keep going.

Being an entrepreneur for over five years has given me some incredible moments big wins, happy clients, and exciting opportunities. But the truth? The hardest moments almost took me out. There was a point where sales were booming, and I was getting back-to-back orders. On the surface, it looked like success. But behind the scenes, it was chaos, burnout was creeping in, my business operations weren’t keeping up, and things like accounting and client response times started slipping through the cracks.  Read more>>

Vic Iddstar Hill

Picture this: I was a nobody living a very unremarkable life in England. Lots of big ideas and big dreams, I was making comics even then, but it was all on a small scale. I was very much of the mindset that big exciting lives happened to *other* people. Read more>>

Erica-Sommer Dudley

I have had a colorful journey of a variety of vocations over the decades including working for my father’s architecture/art firm, a brief stint in retail, a few labels and studios in the record/recording industry, a singing waitress, bartender, promotional/commercial model, a personal assistant at a fine art company, a catering manager for a chain of hotels, while always maintaining my own original music projects. Read more>>

Catherine Ahlin

Entering private practice was a tremendous risk for my family. I’ve been the sole income provider for my family since the beginning and I left a job with a steady income to pursue opening my own practice. I didn’t really know much about running a practice and I wasn’t sure I would be successful. Others I’d worked with weren’t always supportive or encouraging to those going into private practice and I was worried I wouldn’t have enough clients to earn an income. Read more>>

Chrissy Janiga

My journey is based on following my intuition, removing societal pressures, and living a soul-led life. In 2022, I decided to quit drinking alcohol. Once I committed to sobriety, I began to think about purpose and the woman I wanted to become. I had thoughts of writing a book. I had no author or writer experience, but I decided to write a children’s book, I learned about word count and the age to present my book. I’ve now written and published two children’s books. I recently wrote a nonfiction book, Soul-Led Sobriety. Read more>>

Maggie Bahr

I was a risk taker well before I became a business owner, and without the risk taking behavior I’d certainly not have the life I have now. The biggest risk I’ve taken in my life wasn’t starting my business, it was starting my adult life by moving to Germany at 23. I had never travelled to Europe before and didn’t speak German. I spent 11 years in Munich and it transformed the way I saw the world. I returned to the Hudson Valley in 2019 with my husband Benji, and our two young sons. We returned shortly after finding out my mom had been diagnosed with pancreatic cancer. Benji is German and being in the immigration process he couldn’t work here. Our roles needed to change, he became the homeschooling parent and I had to find a job for the first time after becoming a mom. Read more>>

Taniya Robinson

My interest in the spa/wellness industry started over 15 years ago. At the time I was married, raising children, and in the trucking industry as a driver and owner. The stresses of my trucking business kept me in desperate want and need of mental and physical relaxation. The years passed and my longing and interest deepened. I studied a lot about stress on the brain and body, mental health, and various methods to help promote wellness and stress relief. In 2018 all of my studying would be put to the test as I navigated one of the toughest seasons in my life. Read more>>

Dylan Allen

A few years ago, I made a decision that changed everything: I took the risk to independently make Secrets of the Scouts, a raw, investigative film I’d been dreaming about since I was 12. No big company behind me. No grants. No outside funding. Just me—sacrificing time, money, sleep, and comfort to make something real. It was a massive gamble—financially, emotionally, and professionally—but I knew if I didn’t make it, I’d regret it for the rest of my life. Read more>>

Hannah Rose

In 2019, I took the biggest risk of my career—one that would change the trajectory of my life. At the time, I was working in both outpatient and inpatient rehabilitation facilities for substance use disorders. I was doing meaningful work, but I felt a growing sense of restlessness. The rigid structure of these settings left little room for the autonomy and creativity I craved as a therapist. I knew deep in my gut that I needed to do something different, something bold. Read more>>

Judi Bloom

I began as a self taught artist 11 years ago after a 35 year career in the cosmetic Industry, 20 years running Special Events for an International Cosmetic Company. Six years ago I was invited to display and sell my art at the Artists of Scottsdale Ranch Art Show. This was a huge leap for me especially being so new to the art world. All the normal fears went through my head–will anyone like my work? will I sell anything–rejection? Read more>>

Laurie Pohutsky

The biggest risk I’ve ever taken was running for office in 2018. Prior to running, I was a microbiologist. I’m not a complete introvert, strictly speaking, but spending my days in the lab was certainly a far cry from the extremely public scrutiny a campaign brings. But I also saw a need for change and knew that I wasn’t doing enough. I was fearful about what the state of politics meant for reproductive and LGBTQ rights, our environment, and the overall future. Read more>>

Rachel White

Taken from a recent post on Substack, written to my subscribers: “So, our self-funded and self-published TOTEM Tarot Deck has just officially sold out on Amazon. And, while we have the remainder of the copies available on our Etsy Shop, it’s effectively *this close* to being really, truly sold out altogether. Like, forever and ever and ever. It’s kind of weird to think about, actually. Investing the time to create the cards, their art, and the accompanying booklet with artist Emma Cook took several years and was largely an act of faith that maybe, someday, we would print it.  Read more>>